US11505567B2ActiveUtilityA1

Amorphous mixture comprising a neutral mono- or oligosaccharide and an acidic non-carbohydrate component

63
Assignee: GLYCOM ASPriority: Jul 12, 2017Filed: Jul 12, 2018Granted: Nov 22, 2022
Est. expiryJul 12, 2037(~11 yrs left)· nominal 20-yr term from priority
C07H 1/00C07H 3/02A23L 33/40C07H 3/06C13K 13/00A23B 2/92A23B 2/93A23B 2/91
63
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References
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Claims

Abstract

It is provided i) an amorphous carbohydrate with improved chemical stability and/or physical features, ii) a method for producing an amorphous carbohydrate with improved chemical stability and/or physical features, and iii) a method for improving the chemical stability and/or the physical features of an amorphous carbohydrate.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. An amorphous mixture comprising one or more human milk oligosaccharides (HMOs) and one or more acidic non-carbohydrate components, wherein the pH of said mixture in its 5 w/w % aqueous solution at room temperature is around 4.5, and
 wherein the one or more HMOs are selected from the group consisting of 2′-O-fucosyllactose (2′-FL), 3-O-fucosyllactose (3-FL), difucosyllactose (DFL), lacto-N-tetraose (LNT) and lacto-N-neotetraose (LNnT). 
 
     
     
       2. The amorphous mixture according to  claim 1 , consisting essentially of the one or more HMOs and the one or more acidic non-carbohydrate components. 
     
     
       3. The amorphous mixture according to  claim 1 , which is spray-dried or freeze-dried. 
     
     
       4. The amorphous mixture according to  claim 1 , wherein the acidic non-carbohydrate component is an inorganic acid. 
     
     
       5. The amorphous mixture according to  claim 4 , wherein the inorganic acid is selected from the group consisting of sulfuric acid; a monosalt of sulfuric acid; HCl; HBr; nitric acid; phosphoric acid; a monosalt of phosphoric acid; and a disalt of phosphoric acid. 
     
     
       6. The amorphous mixture according to  claim 1 , wherein the acidic non-carbohydrate component is an organic acid. 
     
     
       7. The amorphous mixture according to  claim 6 , wherein the organic acid is selected from the group consisting of formic acid; acetic acid; oxalic acid; tartaric acid; lactic acid; malic acid; and citric acid. 
     
     
       8. A method for making the amorphous mixture according to  claim 1  comprising the steps of:
 a) preparing an aqueous solution of 2′-O-fucosyllactose (2′-FL), 3-O-fucosyllactose (3-FL), difucosyllactose (DFL), lacto-N-tetraose (LNT), lacto-N-neotetraose (LNnT), or a mixture thereof, 
 b) adding one or more acidic non-carbohydrate components to said aqueous solution so that the pH is around −log(x/5·10 −4.5 ), wherein x is the concentration of the neutral oligosaccharide in said aqueous solution after step a) in w/w %, then 
 c) spray-drying or freeze-drying the pH adjusted solution obtained in step b). 
 
     
     
       9. The method according to  claim 8 , wherein the acidic non-carbohydrate component is an inorganic acid. 
     
     
       10. The method according to  claim 9 , wherein the inorganic acid is selected from the group consisting of sulfuric acid; a monosalt of sulfuric acid; HCl; HBr; nitric acid; phosphoric acid; a monosalt of phosphoric acid; and a disalt of phosphoric acid. 
     
     
       11. The method according to  claim 8 , wherein the acidic non-carbohydrate component is an organic acid. 
     
     
       12. The method according to  claim 11 , wherein the organic acid selected from the group consisting of formic acid; acetic acid; oxalic acid; tartaric acid; lactic acid; malic acid; and citric acid. 
     
     
       13. A method for making the amorphous mixture according to  claim 2  comprising the steps of:
 a) preparing an aqueous solution of 2′-O-fucosyllactose (2′-FL), 3-O-fucosyllactose (3-FL), difucosyllactose (DFL), lacto-N-tetraose (LNT), lacto-N-neotetraose (LNnT), or a mixture thereof, 
 b) adding one or more acidic non-carbohydrate components to said aqueous solution so that the pH is around −log(x/5·10 −4.5 ), wherein x is the concentration of the neutral oligosaccharide in said aqueous solution after step a) in w/w %, then 
 c) spray-drying or freeze-drying the pH adjusted solution obtained in step b). 
 
     
     
       14. The method according to  claim 13 , wherein the acidic non-carbohydrate component is an inorganic acid. 
     
     
       15. The method according to  claim 14 , wherein the inorganic acid is selected from the group consisting of sulfuric acid; a monosalt of sulfuric acid; HCl; HBr; nitric acid; phosphoric acid; a monosalt of phosphoric acid; and a disalt of phosphoric acid. 
     
     
       16. The method according to  claim 14 , wherein the organic acid selected from the group consisting of formic acid; acetic acid; oxalic acid; tartaric acid; lactic acid; malic acid; and citric acid. 
     
     
       17. The method according to  claim 13 , wherein the acidic non-carbohydrate component is an organic acid.

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